반응 #73524

반응 방정식

2-phenylbutanedioic acid

H2SO4

toluene

EtOH

→

diethyl 2-phenylbutanedioate

수율 46.0%

반응 조건

후처리

1. 1
   온도is refluxed for 72 hours
2. 2
   농축the reaction mixture is concentrated under reduced pressure
3. 3
   workup.ADDITIONtreated with 300 mL of water
4. 4
   추출extracted with Et2O (2×400 mL)
5. 5
   건조dried over Na2SO4
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue obtained
9. 9
   기타is purified by chromatography on a column of silica gel
10. 10
    세척eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc

실험 절차

In Dean-Stark apparatus, a mixture of 37 g (190.5 mmol) of 2-phenylbutanedioic acid, 6 mL of conc. H2SO4, 80 mL of toluene and 80 mL of EtOH is refluxed for 72 hours. After cooling to room temperature, the reaction mixture is concentrated under reduced pressure and then treated with 300 mL of water, and extracted with Et2O (2×400 mL). The organic phases are combined, dried over Na2SO4, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica gel, eluting with a cyclohexane/EtOAc gradient of 0 to 10% EtOAc. 22 g of diethyl 2-phenylbutanedioate are obtained in the form of an oil.

출처